CN106831781A - A kind of fluorescence probe NASA and its preparation and application - Google Patents

A kind of fluorescence probe NASA and its preparation and application Download PDF

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CN106831781A
CN106831781A CN201510884677.0A CN201510884677A CN106831781A CN 106831781 A CN106831781 A CN 106831781A CN 201510884677 A CN201510884677 A CN 201510884677A CN 106831781 A CN106831781 A CN 106831781A
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fluorescence probe
sahh
nasa
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fluorescence
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贾燕
韩克利
李鹏
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Dalian Institute of Chemical Physics of CAS
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
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    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms

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Abstract

A kind of fluorescence probe NASA and its preparation and application.Can be used to detect the fluorescence probe of external Adenosylhomocysteinase EC3.3.1.1 (S-adenosyl-L-homocysteine hydrolase, abbreviation SAHH) the invention provides one kind.Primary synthetic methods are to be bonded to connect 1,8- naphthalimide generating structures and be by C-S on the site of action adenosine of SAHHCompound；Under SAHH effects, generation

Description

A kind of fluorescence probe NASA and its preparation and application
Technical field
The present invention relates to fluorescence probe field, and in particular to one kind can be used to detect the fluorescence probe of Adenosylhomocysteinase EC3.3.1.1 (S-adenosyl-L-homocysteine hydrolase, abbreviation SAHH).Adenosine molecule is introduced on 1,8- naphthalimides, realizes optionally detecting Adenosylhomocysteinase EC3.3.1.1 using the difference in fluorescence of reactant and product.
Background technology
Adenosylhomocysteinase EC3.3.1.1 (SAHH, EC:3.1.3.1) it is a kind of intracellular enzyme being widely present, it is catalyzed AdoHcy (AdoHcy) hydrolysis generation adenosine and homocysteine.Suppressing SAHH will cause the accumulation of the intracellular mortifier AdoHcy that methylates, so as to produce feedback inhibitory action to transmethylase reaction.And methylate for maintain cell activity be required.In view of core status of the SAHH in the transmethylated reaction of organism is adjusted, it has been selected as the important target spot of various new drug developments, including immunodepressant, antiviral agent, prevents and treats atherosclerosis and Alzheimer disease drugs.The action target spot of the brand-new chemical constitution of SAHH inhibitor, good action effect and uniqueness has caused the extensive interest of domestic and international researcher.
Fluorescence probe is one of means of SAHH in effective detection life entity, has the sensitive advantage of detection compared to absorbance method.One fluorescence probe with application prospect should have before and after effect that change in fluorescence is substantially, fast to target molecule response, selectivity is good, synthesizes simple.It is applied to detect that the fluorescence probe of SAHH is very few at present, access is only shown in the metabolite Hcy using AdoHcy come the method for indirect detection SAHH.Therefore exploitation has very big challenge to the probe of its SAHH.
The content of the invention
The present invention is aiming above mentioned problem, there is provided a kind of fluorescence probe that can be used for the intracellular SAHH of selective enumeration method, and this probe can be acted on optionally with SAHH in physiological conditions, and fluorescence is significantly increased after effect.
The present invention is adopted the following technical scheme that：
Can be used to detect the fluorescence probe of Adenosylhomocysteinase EC3.3.1.1 (S-adenosyl-L-homoc ysteine hydrolase, abbreviation SAHH) the invention provides one kind.Primary synthetic methods are to be bonded to connect 1,8- naphthalimides by C-S on the site of action adenosine of SAHH；The compound generates 4- sulfydryl -1 under SAHH effects, and 8- naphthalimides realize the selective enumeration method to SAHH using the difference of photoluminescent property before and after reaction.
The structure code name NASA of the probe compound of synthesis is represented.
The structural formula I of the fluorescence probe is as follows.
The preparation method of described fluorescence probe is：It is bonded by C-S on the site of action adenosine of SAHH and connects 1,8- naphthalimides；Specific preparation process is as follows,
1) triphenylphosphine (cas is added in dry THF 50ml：603-35-0) 3.76g, stirring is to complete molten.Diethylazodicarboxylate (cas is slowly added dropwise under condition of ice bath, in 5min：1972-28-7)2.2ml.After stirring 30min, 2', 3'- isopropylidene adenosines (cas are added：362-75-4)2.1g.Maintain 0 degree of stirring 10min.Thioacetic acid (cas is slowly added dropwise in 5min：507-09-5)1.0ml.After 0 degree is reacted 1 hour, solvent is spin-dried for, the yellow solid for obtaining column chromatography (CHCl2-MeOH,100:0,95:5,90:10) separate.Obtain compound 11.62g, yield is 65%.
2) in 20ml ethanol, bromo- 1, the 8- naphthalene anhydrides (cas of 4- are added：81-86-7) 1g and 1- butylamine (cas：109-73-9) 353uL, 78 degree are flowed back 4 hours.Solvent is spin-dried for after having reacted, product 2 is obtained1.2g, yield 100%.
3) in dry methyl alcohol, add step 1) in product 1500mg and step 2) in product 453mg, cool to -20 degree, add sodium methoxide (cas：124-41-4)147mg.Solution slowly rises to room temperature, sustained response 20h.Reaction is spin-dried for solvent, column chromatography for separation (CHCl after terminating2-MeOH,100:0,95:5,90:10) product 3, is obtained314mg, yield 40%.
4) in water and formic acid 1:In 1 solution 2ml, 0 degree lower to add step 3) in product 3100mg, slowly rise to room temperature reaction 4h, be warmed to 50 degree of reaction 2h.Solvent is spin-dried for after having reacted.Column chromatography obtains fluorescence probe NASA50mg, yield 53%.
Step 1) described in triphenylphosphine, diethylazodicarboxylate, 2', 3'- isopropylidenes adenosine, thioacetic acid addition be 2:2:1:2；Step 3) in the addition of compound 1 and sodium methoxide be 1:2.2.
The step 1) in, solvent used is anhydrous tetrahydro furan；Described step 1) -4) in stirring mode be magnetic agitation.
Described fluorescence probe can be metabolized by Adenosylhomocysteinase EC3.3.1.1 (S-adenosyl-L-homocys teine hydrolase, abbreviation SAHH) and produce change in fluorescence.After i.e. described fluorescence probe and SAHH effects, fluorescence peak from 500nm blue shifts to 470nm at, and have significant Fluorescence Increasing.
When described fluorescence probe is applied to detection SAHH, its change in fluorescence is because compound of the generation with structure I I；
The probe can be used for the inhibitor screening of Adenosylhomocysteinase EC3.3.1.1.
Beneficial effects of the present invention：
Compound fluorescence in the presence of SAHH is significantly changed, and be can be used for high sensitivity, is detected SAHH with high throughput.Especially, the compound can be used for the inhibitor screening of Adenosylhomocysteinase EC3.3.1.1.
The present invention can be used to detect the fluorescence probe of external Adenosylhomocysteinase EC3.3.1.1 (S-adenosyl-L-homoc ysteine hydrolase, abbreviation SAHH).Primary synthetic methods are to be bonded to connect 1,8- naphthalimide generating structures and be by C-S on the site of action adenosine of SAHHCompound；Under SAHH effects, generationThe detection to SAHH is realized using the difference of photoluminescent property before and after reaction, the probe can be with high sensitivity, with high throughput for the screening of SAHH inhibitor.
Brief description of the drawings
The synthetic route chart of the fluorescence probe NASA provided in Fig. 1 embodiments 1；
The fluorescence probe NASA that Fig. 2 present invention is provided detects the principle schematic of SAHH；
The probe NASA's synthesized in Fig. 3 embodiments 11H NMR (a),13C NMR(b)；
Fluorescence excitation spectrum (a), the emission spectrum (b) of the fluorescence probe NASA aqueous solution in Fig. 4 embodiments 2；
Fluorescence excitation spectrum (a), the emission spectrum (b) of the hydrolysate aqueous solution of fluorescence probe NASA in Fig. 5 embodiments 3；
In Fig. 6 embodiments 4 after fluorescence probe NASA and SAHH response spectrum 470nm peak values with the time linear relationship chart；
Spectrum change figure after fluorescence probe NASA is responded with the SAHH of various concentrations in Fig. 7 embodiments 5；
The dynamics schematic diagram of fluorescence probe NASA and SAHH reaction detection 470nm fluorescence intensities in Fig. 8 embodiments 6；
With fluorescence probe NASA as substrate in Fig. 9 embodiments 7, Dznep can suppress the enzymatic activity of SAHH；
With fluorescence probe NASA as substrate in Figure 10 embodiments 8, the IC50 values of four kinds of inhibitor of SAHH are detected.
Specific embodiment
Following embodiments are used to further illustrate the present invention, but the invention is not restricted to embodiment.
Embodiment 1 (synthesis of probe)：
As shown in figure 1, the synthesis of NASA is divided into 4 steps (as above), compound 1 is accredited as：MS:366.12(positive mode).1HNMR(400MHz,Chloroform-d)δ(ppm):8.37 (s, 1H), 8.19 (s, 1H), 6.07 (d, 1H, J=2.08Hz), 5.77 (s, 2H), 5.51 (d, 1H, J=6.36Hz), 4.97 (d, 1H, J=6.36Hz), 4.34 (t, 1H, J=6.88Hz), 3.29 (d, 1H, J=7.2Hz), 3.08 (d, 1H, J=6.64Hz), 1.60 (s, 3H), 1.39 (s, 3H).The identification of compound 3：MS:575.20(positive mode).1HNMR(400MHz,Chloroform-d)δ(ppm):8.59(d,1H,J=7.28Hz),8.55(d,1H,J=8.48Hz),8.37(d,1H,J=7.76Hz),8.27(s,1H),7.78(s,1H),7.71(t,1H,J=8.16Hz),7.57(d,1H,J=7.8Hz),6.08(s,1H),5.56(d,1H,J=6.2Hz),5.20(d,1H,J=6.12Hz),4.52(t,1H,J=6.76Hz),4.16(t,2H,J=7.64Hz),3.55(m,1H),3.41(m,1H),1.70(m,2H),1.58(s,3H),1.46(m,2H),1.39(s,3H),0.97(t,3H,J=7.32Hz).Target compound NASA (yellow solid).MS:535.17(positive mode).1HNMR(500MHz,Dime thylsulfoxide-d6)δ(ppm):8.53(d,1H,J=8.4Hz),8.52(d,1H,J=6.9Hz),8.36(s,1H),8.32(d,1H,J=7.85Hz),8.13(s,1H),7.87(d,1H,J=8.05Hz),7.83(d,1H,J=8.00Hz),7.26(s,2H),5.93(d,1H,J=5.5Hz),5.56(d,1H,J=5.95Hz),5.43(d,1H,J=5.15Hz),4.87(m,1H),4.33(m,1H),4.18(m,1H),4.03(m,1H),3.75(m,1H),3.68(m,1H),1.61(m,2H),1.35(m,2H),0.92(t,3H,J=7.3Hz).13CNMR(100MHz,Dimethylsulfoxide-d6)δ(ppm):163.10,163.03,156.01,152.53,149.29,143.69,139.95,130.96,130.21,129.63,128.75,127.49,127.19,123.58,122.68,119.16,118.71,87.77,82.19,72.87,72.51,34.19,29.58,19.70,13.61.(Fig. 3 is hydrogen spectrum (a) of compound N ASA, carbon spectrum (b))
Embodiment 2
As shown in figure 4, NASA is dissolved in the PBS of 10mM, the solution of 20uM is configured to.Fluorescence excitation spectrum (a), the fluorescence emission spectrum (b) of the NASA aqueous solution are detected with fluorescence microplate reader (Thermofisher) detector；Maximum excitation/the launch wavelength of result display probe NASA is 400nm/512nm.
Embodiment 3
As shown in figure 5, NI-SH is dissolved in the PBS of 10mM, the solution of 20uM is configured to.Fluorescence excitation spectrum (a), the fluorescence emission spectrum (b) of the NASA aqueous solution are detected with fluorescence microplate reader (Thermofisher) detector；Maximum excitation/the launch wavelength of result display NASA metabolites is 380/470nm.
Embodiment 4：
Add the DMSO solution (500uM) of 2ul NASA, the enzyme (10mg/ml) of 2ul in the PBS of 196ul.Measured using the multi-functional readout instrument of full wavelength scanner formula and 96 hole elisa Plates, sweep an emission spectra within every two minutes.λ ex=380nm, raster width is 5nm, λ em=470nm, at 470nm fluorescent value with the time mapping be it is linear, as a result as shown in Figure 6.
Embodiment 5
By the SAHH enzyme stock concentrations gradient dilutions of 100mg/ml, the enzyme liquid storage of 50/25/10/5/2.5/1/0.5/0.25/0.1mg/ml is obtained.Each reaction adds the enzyme of 2ul NASA (500uM) and 20ul various concentrations in the PBS of 178ul, is measured after being incubated 20min.Measured using the multi-functional readout instrument of full wavelength scanner formula and 96 hole elisa Plates.Measure the fluorescence emission spectrum of the working solution, λ ex=380nm, raster width is 5nm, transmitting boundary is from 400nm-600nm.Result shows such as Fig. 7, and with the growth of enzyme concentration, the fluorescence intensity at 470nm strengthens therewith.
Embodiment 6：
By the SAHH enzyme stock concentrations gradient dilutions of 100mg/ml, the enzyme liquid storage of 50/25/10/5/2.5/1/0.5/0.25/0.1mg/ml is obtained.Each reaction adds the enzyme of 2ul NASA (500uM) and 20ul various concentrations in the PBS of 178ul, and a fluorescent value of 470nm (λ ex=380nm) is swept per 2min at 37 DEG C.Result shows such as Fig. 8, and the fluorescence intensity at 470nm strengthens with the time with enzyme concentration.
Embodiment 7：
Configuration SAHH specific inhibitors Dznep (5mM), add 2ul NASA (500uM) in the PBS of 176ul, the inhibitor of 2ul or the enzyme of 2ul buffer solutions (control) and 20ul, 37 DEG C are incubated lower every 2min and sweep a fluorescent value of 470nm (λ ex=380nm).As Fig. 9, NASA can be completely inhibited by the catalytic action of SAHH by 50uM Dznep (SAHH classics inhibitor), demonstrate again that NA SA are the probe substrates of SAHH.
Embodiment 8：
Configuration NASA specific inhibitors Dznep (5mM)/Adenosine (100mM)/3-deazaadenosine (100mM)/2-Deoxyadenosine (100mM) liquid storage, and ten times of inhibitor liquid storages of dilution, each reacts the inhibitor of the enzyme (10mg/ml) and 2ul that add 2ul NASA (500uM) and 20ul in the PBS (10mM) of 176ul.Measured using the multi-functional readout instrument of full wavelength scanner formula and 96 hole elisa Plates.The fluorescence emission spectrum of the working solution, λ ex=380nm are measured, raster width is 5nm, λ em=470nm.As shown in Figure 10, mapped with log (inhibitor concentration) and enzyme percentage remaining activity, the IC50 values for obtaining four kinds of compounds are respectively Dznep：0.88uM；Adenosine:8.02uM；2’-De oxyadenosine 56.77uM；3’-Deazaadenosine 11.02uM.

Claims (7)

1. a kind of fluorescence probe NASA, it is characterised in that：The structure of described fluorescence probe Shown in structure I,
Structure code name：NASA；
R can for hydrogen atom or can also be with the 1-10 substitution alkyl of carbon atom, Or phenyl or substituted-phenyl, the substitution base on substituted-phenyl is the alkyl of C1-C5, on phenyl The number of base is replaced to be 1-5.
2. the application of fluorescence probe according to claim 1, it is characterised in that：It is described Fluorescence probe be applied to detection SAHH when, its change in fluorescence because generation have structure The compound of II；
3. the application of the fluorescence probe described in a kind of claim 1, it is characterised in that：It is described Fluorescence probe can be used for Adenosylhomocysteinase EC3.3.1.1 The detection of (S-adenosyl-L-homocysteine hydrolase, abbreviation SAHH).
4. the application of the fluorescence probe described in a kind of claim 3, it is characterised in that：It is described Fluorescence probe can be used for detect cell in SAHH.
5. the application of fluorescence probe according to claim 3, the probe can be used for S- The inhibitor screening of SAHH.
6. the application of fluorescence probe according to claim 3, the probe can be used for from The quantitative determination of Adenosylhomocysteinase EC3.3.1.1 in body erythrocyte.
7. a kind of preparation method of fluorescence probe described in claim 1, its specific preparation process It is as follows,
1) triphenylphosphine (cas is added in dry THF 50ml：603-35-0) 3.76g, stirs Mix to complete molten, diethylazodicarboxylate (cas is slowly added dropwise under condition of ice bath, in 5min： 1972-28-7) 2.2ml, after stirring 30min, adds 2', 3'- isopropylidene adenosines (cas：362-75-4) 2.1g, maintains 0 DEG C of stirring 10min, and thioacetic acid (cas is slowly added dropwise in 5min：507-09-5) 1.0ml, after 0 DEG C is reacted 1 hour, is spin-dried for solvent, the yellow solid for obtaining column chromatography (CHCl2 - MeOH, 100:0,95:5,90:10) separate, obtain compound 11.62g, Yield is 65%；
2) in 20ml ethanol, bromo- 1, the 8- naphthalene anhydrides (cas of 4- are added：81-86-7) 1g and 1- Butylamine (cas：109-73-9) 353uL, 78 DEG C are flowed back 4 hours, and solvent is spin-dried for after having reacted, Obtain product 21.2g, yield 100%；
3) in dry methyl alcohol, add step 1) in product 1500mg and step 2) in Product 453mg, cools to -20 DEG C, adds sodium methoxide (cas：124-41-4) 147mg, it is molten Liquid slowly rises to room temperature, sustained response 20h；Reaction is spin-dried for solvent, column chromatography point after terminating From (CHCl2-MeOH,100:0,95:5,90:10) product 3, is obtained314mg, yield 40%；
4) in water and formic acid 1:In 1 solution 2ml, at 0 DEG C add step 3) in product 3 100mg, slowly rises to room temperature reaction 4h, is warmed to 50 DEG C of reaction 2h, rotation after having reacted Dry solvent, column chromatography obtains fluorescence probe NASA50mg, yield 53%.
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Publication number Priority date Publication date Assignee Title
CN109400529A (en) * 2018-12-05 2019-03-01 安庆北化大科技园有限公司 Suitable for the naphthalimide aryl benzyl thioether-type photoinitiator and preparation method of UV-LED photocuring and application
CN109400529B (en) * 2018-12-05 2022-04-08 安庆北化大科技园有限公司 Naphthalimide aryl benzyl thioether type photoinitiator suitable for UV-LED photocuring, and preparation method and application thereof

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